Probably doesn't help (not just him but probably a bunch of players) that they have never known a debt in their lives other than overdue books from the library (which I'm sure was covered for him) or that just because you got paid means the money will always be there.
Like you said, $14M is probably 3x more than I would need to live a decent life for the next 50 years (and I know I'm not gonna live 50 more years so I'll have some left over for my kids).